CN107614650B - Adhesive composition - Google Patents
Adhesive composition Download PDFInfo
- Publication number
- CN107614650B CN107614650B CN201680028674.XA CN201680028674A CN107614650B CN 107614650 B CN107614650 B CN 107614650B CN 201680028674 A CN201680028674 A CN 201680028674A CN 107614650 B CN107614650 B CN 107614650B
- Authority
- CN
- China
- Prior art keywords
- compound
- aluminum chelate
- anisotropic conductive
- adhesive composition
- silanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 86
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 71
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000013522 chelant Substances 0.000 claims abstract description 45
- -1 thiol compound Chemical class 0.000 claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 13
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 10
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 238000012695 Interfacial polymerization Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 239000002245 particle Substances 0.000 claims description 53
- 239000004593 Epoxy Substances 0.000 claims description 35
- 239000004925 Acrylic resin Substances 0.000 claims description 25
- 229920000178 Acrylic resin Polymers 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910000679 solder Inorganic materials 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 238000005259 measurement Methods 0.000 description 40
- 238000011156 evaluation Methods 0.000 description 31
- 239000000654 additive Substances 0.000 description 20
- 230000000996 additive effect Effects 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000003553 thiiranes Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 230000020169 heat generation Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000000919 ceramic Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- LABQKWYHWCYABU-UHFFFAOYSA-N 4-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCCCOC(=O)CC(C)S LABQKWYHWCYABU-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- MQPPCKJJFDNPHJ-UHFFFAOYSA-K aluminum;3-oxohexanoate Chemical compound [Al+3].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O MQPPCKJJFDNPHJ-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical class CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- GRYZINPXJPRKAI-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hept-4-en-4-ylmethyl 7-oxabicyclo[4.1.0]hept-4-ene-4-carboxylate Chemical compound C=1C2OC2CCC=1C(=O)OCC(CC1)=CC2C1O2 GRYZINPXJPRKAI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910016338 Bi—Sn Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VMMPFJWRJCVIMT-UHFFFAOYSA-L C(C)CC(CC(=O)[O-])=O.C(C)CC(CC(=O)[O-])=O.C(C)(=O)CC([CH2-])=O.[Al+3] Chemical compound C(C)CC(CC(=O)[O-])=O.C(C)CC(CC(=O)[O-])=O.C(C)(=O)CC([CH2-])=O.[Al+3] VMMPFJWRJCVIMT-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910020816 Sn Pb Inorganic materials 0.000 description 1
- 229910020836 Sn-Ag Inorganic materials 0.000 description 1
- 229910020888 Sn-Cu Inorganic materials 0.000 description 1
- 229910020922 Sn-Pb Inorganic materials 0.000 description 1
- 229910020935 Sn-Sb Inorganic materials 0.000 description 1
- 229910020988 Sn—Ag Inorganic materials 0.000 description 1
- 229910019204 Sn—Cu Inorganic materials 0.000 description 1
- 229910018956 Sn—In Inorganic materials 0.000 description 1
- 229910008783 Sn—Pb Inorganic materials 0.000 description 1
- 229910008757 Sn—Sb Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- UGFDIXXDKBKDSR-UHFFFAOYSA-N di(propan-2-yl)aluminum Chemical compound CC(C)[Al]C(C)C UGFDIXXDKBKDSR-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/70—Chelates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/04—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/62—Arrangements for conducting electric current to or from the semiconductor body, e.g. lead-frames, wire-bonds or solder balls
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/15—Structure, shape, material or disposition of the bump connectors after the connecting process
- H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump connector
- H01L2224/161—Disposition
- H01L2224/16151—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/16221—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/16225—Disposition the bump connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
- H01L2224/732—Location after the connecting process
- H01L2224/73201—Location after the connecting process on the same surface
- H01L2224/73203—Bump and layer connectors
- H01L2224/73204—Bump and layer connectors the bump connector being embedded into the layer connector
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Power Engineering (AREA)
- Computer Hardware Design (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Conductive Materials (AREA)
- Epoxy Resins (AREA)
- Led Device Packages (AREA)
- Wire Bonding (AREA)
- Organic Insulating Materials (AREA)
- Non-Insulated Conductors (AREA)
Abstract
An adhesive composition which can achieve not only excellent life performance but also a wide mounting range, comprising: a cationically polymerizable compound, an aluminum chelate-silanol-based curing catalyst, and a nucleophilic compound containing a sulfur atom having a non-shared electron pair. The nucleophilic compound is a thiol compound or an episulfide compound. The aluminum chelate-silanol-based curing catalyst comprises an aluminum chelate curing agent and a silanol compound or a silane coupling agent. The aluminum chelate curing agent is a latent aluminum chelate curing agent held in a porous resin obtained by interfacial polymerization of a polyfunctional isocyanate compound.
Description
Technical Field
The present invention relates to an adhesive composition containing an aluminum chelate-silanol-based curing catalyst.
Background
Conventionally, an aluminum chelate compound-silanol curing catalyst has been known, in which an aluminum chelate compound curing agent interacts with a silane coupling agent (or silanol compound) to cationically polymerize an epoxy compound (for example, see patent document 1). In the aluminum chelate compound-silanol curing catalyst, a cationic species and an anionic species coexist as active species.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2009-197206.
Disclosure of Invention
Problems to be solved by the invention
In the aluminum chelate compound-silanol curing catalyst, since a cationic species and an anionic species coexist as active species, stability is low and it is difficult to obtain excellent life performance. In addition, since the aluminum chelate compound-silanol-based curing catalyst has a rapid curing reaction, it is necessary to control the temperature distribution during thermocompression bonding.
The present invention is directed to solving the above-described problems of the prior art, and its object is to: provided is an adhesive composition which can obtain not only excellent life performance but also a wide mounting range (margin).
Means for solving the problems
As a result of intensive studies, the present inventors have found that: by blending a nucleophilic compound containing a sulfur atom having an unshared electron pair, not only is life performance improved, but also a wide mounting range is obtained.
That is, the pressure-sensitive adhesive composition according to the present invention is characterized by containing a cationically polymerizable compound, an aluminum chelate-silanol-based curing catalyst, and a nucleophilic compound containing a sulfur atom having a non-shared electron pair.
Further, a light-emitting device according to the present invention includes: the anisotropic conductive film is a cured product of an anisotropic conductive adhesive containing a cationically polymerizable compound, an aluminum chelate-silanol curing catalyst, and a nucleophilic compound containing a sulfur atom having a non-shared electron pair.
Effects of the invention
According to the present invention, by adding a nucleophilic compound containing a sulfur atom having an unshared electron pair, the stability of an aluminum chelate-silanol-based curing catalyst can be improved while delaying the curing reaction, and thus excellent life performance and a wide mounting range can be obtained.
Drawings
FIG. 1 is a graph showing an example of Differential Scanning Calorimeter (DSC) measurement of an aluminum chelate compound-silanol curing catalyst to which a nucleophilic compound is added.
FIG. 2 is a graph showing an example of Differential Scanning Calorimeter (DSC) measurement of a conventional aluminum chelate compound-silanol curing catalyst.
FIG. 3 is a sectional view showing a sea-island model in which a sea is formed of an epoxy compound and islands are formed of an acrylic resin.
Fig. 4 is a cross-sectional view showing an example of the light-emitting device.
FIG. 5 is a view for explaining a process of producing an LED mounting sample.
Fig. 6 is a graph showing temperature distributions of 180 c-10 seconds and 180 c-30 seconds.
Fig. 7 is a cross-sectional view showing an outline of a wafer shear strength (die shear strip) test.
Fig. 8 is a sectional view showing an outline of a 90-degree peel strength test.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail in the following order with reference to the drawings.
1. Adhesive composition
2. Light emitting device
3. Examples of the embodiments
< 1. adhesive composition >
The adhesive composition according to the present embodiment contains: a cationically polymerizable compound, an aluminum chelate-silanol-based curing catalyst, and a nucleophilic compound containing a sulfur atom having an unshared electron pair.
As shown in the following formulas (1) and (2), in the aluminum chelate-silanol-based curing catalyst, an aluminum chelate curing agent interacts with a silane coupling agent (or silanol compound) to generate cationic species and anionic species, and the cationically polymerizable compound is cationically polymerized.
In the present embodiment, by adding the nucleophilic compound containing a sulfur atom having an unshared electron pair, the stability of the aluminum chelate compound-silanol-based curing catalyst can be improved, and the curing reaction can be delayed, so that excellent life performance and a wide mounting range can be obtained.
Fig. 1 is a graph showing an example of Differential Scanning Calorimeter (DSC) measurement of an aluminum chelate compound-silanol curing catalyst to which a nucleophilic compound is added, and fig. 2 is a graph showing an example of Differential Scanning Calorimeter (DSC) measurement of a conventional aluminum chelate compound-silanol curing catalyst.
As is clear from fig. 1 and 2, the addition of the nucleophilic compound can shift the highest (peak) reaction temperature to the high temperature side. Specifically, the reaction end temperature may be the same, and the reaction start temperature and the reaction maximum temperature may be delayed. Since the reaction end point temperature is the same, the mounting conditions do not need to be changed, and the manufacturing time does not extend. In addition, since the reaction start temperature is relatively late, the room temperature life of the adhesive can be extended. Further, since the reaction maximum temperature is relatively late, the time for wetting into a base material such as aluminum becomes long, and the adhesive force can be improved. The reason for this is considered to be: at room temperature, the nucleophilic compound coordinates with the aluminum chelate curing agent to form a stable state, and the coordination of the nucleophilic compound is released from the aluminum chelate curing agent by heating, and the reactions of the above formulas (1) and (2) start to proceed. This can also be presumed from the following: as shown in fig. 1, when the highest reaction temperature is shifted to a high temperature side and then the mercapto-based coupling agent is hydrolyzed in a humidity environment, the mercapto-based coupling agent is added as a nucleophilic compound, and then the reaction returns to a state where the mercapto-based coupling agent is not added, as shown in fig. 2.
In the binder composition to which the nucleophilic compound is added, it is preferable that the reaction peak temperature at a temperature increase rate of 10 ℃/min in the differential scanning calorimeter is 50 ℃ or higher than the reaction start temperature. Since the curing reaction is slowed by increasing the reaction peak temperature by 50 ℃ or more than the reaction start temperature, the base material and the resin can be fused even under the thermocompression bonding condition with a steep temperature rise curve, and high wafer shear strength and peel strength can be obtained. Therefore, excellent bonding properties can be obtained regardless of the thermocompression bonding condition in which the temperature rise curve is steep or the thermocompression bonding condition in which the temperature rise curve is slow, and the mounting range can be expanded. The reaction peak temperature can be controlled by the number of SH groups in the nucleophilic compound, the amount of the added SH group, and the like.
The following describes the cationically polymerizable compound, the aluminum chelate-silanol curing catalyst, and the nucleophilic compound.
[ cationically polymerizable Compound ]
The cationic polymerizable compound is a compound having a functional group that is polymerizable by cationic species. Examples of the cationically polymerizable compound include: epoxy compounds, vinyl ether compounds, cyclic ether compounds, etc., and 1 or 2 or more of these may be used. Among these, epoxy compounds are preferably used.
Examples of the epoxy compound include: alicyclic epoxy compounds, bisphenol type epoxy resins derived from epichlorohydrin and bisphenol a or bisphenol F, polyglycidyl ethers, polyglycidyl esters, aromatic epoxy compounds, novolak type epoxy compounds, glycidyl amine type epoxy compounds, glycidyl ester type epoxy compounds, and the like, and 1 or 2 or more of these can be used. Among these, it is preferable to use an alicyclic epoxy compound or a hydrogenated epoxy compound in which an addition reaction to the β -position carbon due to a silanol anion generated from a silane coupling agent does not easily occur.
As the alicyclic epoxy compound, there can be preferably mentioned: an alicyclic epoxy compound having 2 or more epoxy groups in the molecule. These may be liquid or solid. Specifically, there may be mentioned: 3, 4-epoxycyclohexenecarboxylic acid 3, 4-epoxycyclohexenylmethyl ester, glycidyl hexahydrobisphenol A, and the like. Among these, 3, 4-epoxycyclohexenylmethyl-3 ',4' -epoxycyclohexene carboxylate is preferably used from the viewpoint that the cured product can secure Light transmittance suitable for mounting LED (Light Emitting Diode) elements and the like and is excellent in rapid curability.
As the hydrogenated epoxy compound, there can be used: the hydrogenated product of the alicyclic epoxy compound is a hydrogenated epoxy compound obtained by hydrogenating a known epoxy compound such as bisphenol a type or bisphenol F type.
[ aluminum chelate compound-silanol curing catalyst ]
The aluminum chelate-silanol-based curing catalyst comprises an aluminum chelate curing agent and a silanol compound.
As the aluminum chelate curing agent, known aluminum chelate curing agents can be used, and for example, it is preferable to use: a complex represented by formula (3) wherein 3 beta-keto-enol anions are coordinated to aluminum.
Herein, R is1、R2And R3Each independently is an alkyl or alkoxy group. Examples of the alkyl group include: methyl, ethyl, and the like. Examples of the alkoxy group include: methoxy, ethoxy, oleyloxy (oleyloxy), and the like.
Specific examples of the aluminum chelate curing agent represented by the formula (3) include: tris (acetylacetonate) aluminum, tris (ethylacetoacetate) aluminum, monoacetylacetonebis (ethylacetoacetate) aluminum, monoacetylacetonebialoleyl acetate, ethylacetoacetate diisopropylaluminum, alkylacetoacetate) diisopropylaluminum, and the like.
Examples of the silanol compound include: an aryl silanol represented by the formula (4).
Wherein m is 2 or 3, and the sum of m and n is 4. The silanol compound represented by formula (4) is a monoalcohol or a diol. "Ar" is an aryl group which may be substituted; examples of the aryl group include: phenyl, naphthyl, anthracenyl, azulenyl, fluorenyl, thienyl, furyl, pyrrolyl, imidazolyl, pyridyl and the like. Among them, a phenyl group is preferable from the viewpoint of easiness in obtaining and obtaining cost. The m Ar groups may be the same or different, and are preferably the same from the viewpoint of acquisition easiness.
These aryl groups may have 1 to 3 substituents, and examples thereof include: halogen such as chlorine and bromine, alkoxycarbonyl such as trifluoromethyl, nitro, sulfo, carboxyl, methoxycarbonyl and ethoxycarbonyl, and electron-withdrawing groups such as formyl; and an electron donating group such as an alkyl group such as a methyl group, an ethyl group, or a propyl group, an alkoxy group such as a methoxy group or an ethoxy group, a monoalkylamino group such as a hydroxyl group, an amino group, or a monomethylamino group, or a dialkylamino group such as a dimethylamino group. It is noted that the acidity of the hydroxyl group of silanol can be increased by using an electron-withdrawing group as a substituent, and conversely, the acidity can be decreased by using an electron-donating group, so that the curing activity can be controlled. Here, the substituents of m Ar may be different, but it is preferable that m Ar have the same substituent from the viewpoint of acquisition easiness. In addition, only a part of Ar may have a substituent, and no substituent may be present in the other Ar.
Among the silanol compounds of formula (4), preferred compounds include: triphenyl silanol or diphenyl silanol. A particularly preferred compound is triphenyl silanol.
In addition, the aluminum chelate curing agent and the silanol compound are preferably: a latent aluminum chelate curing agent which is retained in a porous resin obtained by interfacial polymerization of a polyfunctional isocyanate compound. The latent aluminum chelate curing agent can be obtained by adding an oil phase obtained by dissolving and dispersing an aluminum chelate curing agent, a polyfunctional isocyanate compound, a radical polymerizable compound, a radical polymerization initiator and a silanol compound in an organic solvent to an aqueous phase containing a dispersant, heating and stirring the mixture to cause interfacial polymerization of the polyfunctional isocyanate compound and to cause radical polymerization of the radical polymerizable compound, thereby allowing the aluminum chelate curing agent and the silanol compound to be retained in the obtained porous resin.
The polyfunctional isocyanate compound preferably has 2 or more isocyanate groups in 1 molecule, and more preferably has 3 isocyanate groups in 1 molecule. Examples of the trifunctional isocyanate compound include: a TMP adduct of formula (5) obtained by reacting 1 mole of trimethylolpropane with 3 moles of a diisocyanate compound; an isocyanurate body of the formula (6) obtained by self-condensing 3 moles of a diisocyanate compound; and a biuret product (ピュウレット product) of the formula (7) obtained by condensing 2 moles of diisocyanate urea obtained from 3 moles of diisocyanate compounds with the remaining 1 mole of diisocyanate.
In the above formulas (5) to (7), the substituent R is a moiety obtained by removing an isocyanate group of a diisocyanate compound. Specific examples of such diisocyanate compounds include: toluene 2, 4-diisocyanate, toluene 2, 6-diisocyanate, m-xylylene diisocyanate, hexamethylene diisocyanate, hexahydro m-xylylene diisocyanate, isophorone diisocyanate, methylene diphenyl-4, 4' -diisocyanate, and the like.
By using such a latent aluminum chelate complex curing agent comprising a porous resin and an aluminum chelate complex curing agent held in the pores thereof, the storage stability can be greatly improved even when the agent is blended directly into a cationically polymerizable compound and is in a mono-liquefied state.
If the content of the aluminum chelate curing agent is too small, the curing agent cannot be sufficiently cured, and if it is too large, the resin characteristics (for example, crosslinkability) of a cured product of the adhesive composition tend to be lowered, and therefore, it is preferably 0.1 to 30 parts by mass, more preferably 1 to 10 parts by mass, per 100 parts by mass of the cationically polymerizable compound.
In addition, the aluminum chelate-silanol-based curing catalyst may also include the above-described aluminum chelate curing agent and silane coupling agent.
The silane coupling agent has the function of initiating cationic polymerization by interacting with an aluminum chelate curing agent, particularly a latent aluminum chelate curing agent. As such a silane coupling agent, preferred are: the cationic polymerizable resin composition contains 1 to 3 lower alkoxy groups in the molecule and has a group reactive with a functional group of the cationic polymerizable resin, such as a vinyl group, a styryl group, an acryloyloxy group, a methacryloyloxy group, an epoxy group, an amino group, or the like. The coupling agent having an amino group can be used in the case where the cationic species generated by the aluminum chelate compound-silanol-based curing catalyst is not substantially captured.
Examples of such a silane coupling agent include: vinyltris (beta-methoxyethoxy) silane, vinyltriethoxysilane, vinyltrimethoxysilane, gamma-styryltrimethoxysilane, gamma-methacryloxypropyltrimethoxysilane, gamma-acryloxypropyltrimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropylmethyldiethoxysilane, N-beta- (aminoethyl) -gamma-aminopropyltrimethoxysilane, N-beta- (aminoethyl) -gamma-aminopropylmethyldimethoxysilane, gamma-aminopropyltriethoxysilane, N-phenyl-gamma-aminopropyltrimethoxysilane, gamma-glycidyloxypropyltrimethoxysilane, gamma-glycidyloxyethylmethyldimethoxysilane, gamma-glycidyloxyethyl, Gamma-chloropropyltrimethoxysilane, and the like.
If the content of the silane coupling agent is too small, curability tends to decrease, and if it is too large, resin characteristics (for example, storage stability) of a cured product of the composition tend to decrease, and therefore, it is preferably 0.1 to 30 parts by mass, and more preferably 1 to 10 parts by mass, per 100 parts by mass of the cationically polymerizable compound.
In addition, the aluminum chelate curing agent is preferably: a latent aluminum chelate curing agent which is retained in a porous resin obtained by interfacial polymerization of a polyfunctional isocyanate compound. The latent aluminum chelate curing agent can be produced by: a solution obtained by dissolving an aluminum chelate curing agent and a polyfunctional isocyanate compound in a volatile organic solvent is poured into an aqueous phase containing a dispersant, and interfacial polymerization is carried out by heating and stirring.
[ nucleophilic Compound ]
The nucleophilic compound comprises a sulfur atom having an unshared pair of electrons. Thereby, the reaction peak temperature in the differential scanning calorimeter of the adhesive composition can be shifted to a high temperature side higher by 50 ℃ or more than the reaction start temperature. The reason for this is that: it is considered that the nucleophilic compound is coordinated to the aluminum chelate curing agent at room temperature to form a stable state, and is released from the aluminum chelate curing agent by heating. Further, since the curing reaction strain is slow, the base material and the resin can be fused even under the thermocompression bonding condition having a steep temperature rise curve, and high wafer shear strength and peel strength can be obtained.
Examples of the nucleophilic compound include: thiol compounds, episulfide compounds, and the like. Examples of the thiol compound include: mercaptosilanes such as mercaptoalkyl-alkoxysilanes including 3-mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane; mercaptoalkanoic acid esters represented by 3-mercaptobutanoic acid ester or propionate derivatives such as 1, 4-bis (3-mercaptobutanoyloxy) butane, pentaerythritol tetrakis (3-mercaptobutanoate) and pentaerythritol tetrakis (3-mercaptopropionate). Examples of commercially available products of the 3-mercaptobutyrate derivative include: trade names "Karenz MT BD 1" (Showa electrician (Karenz) strain), "Karenz MT PE 1" (Showa electrician (Karenz) strain), and the like. Examples of the episulfide compound include: an episulfide compound or hydrogenated episulfide compound having 1 or more kinds of skeletons selected from a chain aliphatic skeleton, an aliphatic cyclic skeleton, and an aromatic skeleton.
In addition, the thiol compound preferably has 2 or more mercapto groups (SH groups) in 1 molecule, and the episulfide compound preferably has 2 or more episulfide groups (episulfide groups) in 1 molecule. The larger the number of functional groups such as mercapto groups and episulfide groups, the larger the shift of the reaction peak tends to be.
If the content of the nucleophilic compound is too small, the effect of improving stability cannot be obtained, and if it is too large, the cationic species generated by the aluminum chelate-silanol curing catalyst may be trapped, and therefore, the amount is preferably 0.1 to 100 parts by mass, more preferably 0.5 to 50 parts by mass, per 100 parts by mass of the cationically polymerizable compound.
[ other ingredients ]
The pressure-sensitive adhesive composition according to the present embodiment may contain, as another component, an acrylic resin, preferably a copolymer of acrylic acid and a hydroxyl group-containing acrylate. Thereby, a high adhesive force can be obtained even for the aluminum wiring forming a passive state on the surface. Preferred copolymers include: 0.5 to 10wt% of acrylic acid and 0.5 to 10wt% of acrylate having a hydroxyl group, and the weight average molecular weight is 50000 to 900000.
Fig. 3 is a cross-sectional view showing a sea-island pattern in the case where the epoxy compound is used as a sea and the acrylic resin is used as an island in the interface between the adhesive and the oxide film. The sea-island pattern is a cured product pattern showing a state in which islands 13 of an acrylic resin dispersed in a sea 12 of an epoxy compound are in contact with an oxide film 11a of a wiring 11.
In the cured product mold, acrylic acid reacts with the epoxy compound to connect islands 13 of the acrylic resin with sea 12 of the epoxy compound, and roughens the surface of the oxide film 11a to enhance the effect of fixation (anchor) with the sea 12 of the epoxy compound. In addition, the acrylate having a hydroxyl group obtains electrostatic adhesive force to the wiring 11 due to the polarity of the hydroxyl group. By thus bonding the entire oxide film 11a with the cured product of the islands 13 of the acrylic resin and the sea 12 of the epoxy compound, excellent adhesive force can be obtained. The cured product model shown in fig. 3 shows that the weight average molecular weight of the acrylic resin is correlated with the size of the islands 13 of the acrylic resin, and the islands 13 of the acrylic resin having an appropriate size can be brought into contact with the oxide film 11a by the weight average molecular weight of the acrylic resin being 50000 to 900000. When the weight average molecular weight of the acrylic resin is less than 50000, the contact area between the islands 13 of the acrylic resin and the oxide film 11a becomes small, and the effect of improving the adhesive force cannot be obtained. When the weight average molecular weight of the acrylic resin exceeds 900000, the islands 13 of the acrylic resin become large, and the oxide film 11a is not likely to adhere to the entire cured product of the islands 13 of the acrylic resin and the sea 12 of the epoxy compound, resulting in a decrease in adhesive force.
In addition, the acrylic resin may be formed from a raw material containing 0.5 to 10wt% of acrylic acid, more preferably 1 to 5wt% of acrylic acid. By containing 0.5 to 10wt% of acrylic acid, the islands 13 of the acrylic resin are connected with the sea 12 of the epoxy compound by the reaction with the epoxy compound, and the surface of the oxide film 11a is roughened to enhance the fixing effect with the sea 12 of the epoxy compound.
In addition, the acrylic resin may be formed from a raw material containing 0.5 to 10wt% of an acrylate having a hydroxyl group, more preferably 1 to 5wt% of an acrylate having a hydroxyl group. The adhesive force to the wiring 11 is electrostatically obtained by containing 0.5 to 10wt% of acrylate having a hydroxyl group due to the polarity of the hydroxyl group.
As the acrylate having a hydroxyl group, there may be mentioned: 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and the like. Among these, 2-hydroxyethyl methacrylate which is excellent in adhesion to an oxide film is preferably used.
In addition, the acrylic resin may be formed from a raw material containing an acrylate having no hydroxyl group in addition to acrylic acid and an acrylate having a hydroxyl group. Examples of the acrylate having no hydroxyl group include: butyl acrylate, ethyl acrylate, acrylonitrile, and the like.
The content of the acrylic resin is preferably 1 to 10 parts by mass, more preferably 1 to 5 parts by mass, based on 100 parts by mass of the epoxy compound. This makes it possible to obtain a cured product in which the islands 13 of the acrylic resin are dispersed in the sea 12 of the epoxy compound at a good density.
The pressure-sensitive adhesive composition according to the present embodiment may contain an inorganic filler as another component for the purpose of controlling flowability and improving particle capture rate. The inorganic filler is not particularly limited, but may be: silica, talc, titanium oxide, calcium carbonate, magnesium oxide, and the like. Such an inorganic filler can be suitably used for the purpose of relaxing the stress of a connection structure connected by an adhesive. In addition, a softening agent such as a thermoplastic resin or a rubber component may be blended.
According to the adhesive composition, high adhesive force can be obtained for metals which are difficult to adhere, such as aluminum.
In addition, the adhesive composition may be an anisotropic conductive adhesive containing conductive particles. As the conductive particles, known conductive particles can be used. Examples thereof include: particles of various metals or metal alloys such as nickel, iron, copper, aluminum, tin, lead, chromium, cobalt, silver, and gold; particles obtained by coating metal on the surface of particles of metal oxide, carbon, graphite, glass, ceramic, plastic, or the like; and particles obtained by further coating an insulating film on the surfaces of these particles. In the case of particles obtained by coating a metal on the surface of resin particles, the resin particles may be, for example: epoxy resins, phenol resins, acrylic resins, acrylonitrile/styrene (AS) resins, benzoguanamine resins, divinylbenzene resins, styrene resins, and the like. In addition, in order to suppress an increase in resistance against flat deformation of the conductive particles, the surfaces of the resin particles may be coated with Ni or the like. Among these, conductive particles in which a metal layer is formed on the surface of resin particles are preferably used. According to such conductive particles, since the conductive particles are easily broken and easily deformed when compressed, the contact area with the wiring pattern can be increased. In addition, variations in the height of the wiring pattern can be absorbed.
The average particle diameter of the conductive particles is preferably 1 μm or more and 10 μm or less, and more preferably 1 μm or more and 8 μm or less. From the viewpoint of connection reliability and insulation reliability, the amount of the conductive particles to be incorporated is preferably 1 part by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the epoxy compound.
Further, it is preferable to use the conductive particles in combination with the solder particles. The solder particles are preferably smaller than the average particle diameter of the conductive particles, and the average particle diameter of the solder particles is preferably 20% or more and less than 100% of the average particle diameter of the conductive particles. If the solder particles are too small relative to the conductive particles, the solder particles are not captured between the opposing terminals during pressure bonding, and no metal bonding occurs, so that excellent heat dissipation characteristics and electrical characteristics cannot be obtained. On the other hand, if the solder particles are too large relative to the conductive particles, for example, shoulder contact by the solder particles occurs at the edge portion of the LED chip, and leakage occurs, which deteriorates the yield of the product.
The solder particles can be selected from, for example, Sn-Pb, Pb-Sn-Sb, Sn-Pb-Bi, Bi-Sn, Sn-Cu, Sn-Pb-Cu, Sn-In, Sn-Ag, Sn-Pb-Ag, etc., as defined In JIS Z3282-1999, depending on the electrode material, the connection conditions, etc. The shape of the solder particles may be appropriately selected from granular shapes, scaly shapes, and the like. In order to improve the anisotropy, the solder particles may be covered with an insulating layer.
The blending amount of the solder particles is preferably 1 vol% or more and 30 vol% or less. When the amount of the solder particles blended is too small, excellent heat dissipation characteristics cannot be obtained, and when the amount blended is too large, anisotropy is impaired, and excellent connection reliability cannot be obtained.
According to the anisotropic conductive adhesive, excellent connection reliability can be obtained for metals which are difficult to adhere, such as aluminum.
< 2. light emitting device
Next, a light-emitting device to which the present invention is applied will be described. Fig. 4 is a cross-sectional view showing an example of the light-emitting device. The light emitting device includes: a substrate 21 having a wiring pattern 22, an anisotropic conductive film 30 formed on an electrode of the wiring pattern 22, and a light-emitting element 23 mounted on the anisotropic conductive film 30, wherein the anisotropic conductive film 30 is composed of a cured product of the aforementioned anisotropic conductive adhesive. The light-emitting device is obtained by: the anisotropic conductive adhesive described above is applied between the wiring pattern 22 on the substrate 21 and the bumps (bump)26 for connection formed on the n-electrode 24 and the p-electrode 25 of the LED element as the light emitting element 23, respectively, to flip-chip mount the substrate 21 and the light emitting element 23.
In the present embodiment, by using the anisotropic conductive adhesive, a substrate having a wiring pattern made of aluminum can be suitably used. Thus, the cost of the LED product can be reduced.
If necessary, the entire light-emitting element 23 may be sealed with a transparent mold resin so as to cover it. Further, a light reflecting layer may be provided on the light emitting element 23. As the light emitting element, a known light emitting element may be used in addition to the LED element within a range in which the effect of the present invention is not impaired.
Examples
< 3. example >
Hereinafter, embodiment 1 of the present invention will be described.
< embodiment 1 >
In example 1, an anisotropic conductive adhesive containing various additives was prepared. Then, the reaction start temperature and the reaction peak temperature of the anisotropic conductive adhesive were measured. In addition, the lifetime of the anisotropic conductive adhesive was evaluated. Further, an LED chip was mounted on a substrate using an anisotropic conductive adhesive, an LED mounting sample was prepared, and the chip shear strength thereof was measured. In addition, the peel strength of the anisotropic conductive adhesive was measured. It should be noted that the present invention is not limited to these examples.
[ production of Anisotropic conductive adhesive ]
An anisotropic conductive adhesive was prepared by mixing a predetermined amount of any of the additives shown in table 1. 100 parts by mass of AN alicyclic epoxy compound (trade name: Celloxide 2021P, (manufactured by Daicel, Ltd.), 5 parts by mass of a latent aluminum chelate curing agent, 5 parts by mass of AN acrylic resin (butyl acrylate (BA): 15wt%, Ethyl Acrylate (EA): 63wt%, Acrylonitrile (AN): 20wt%, Acrylic Acid (AA): 1wt%, 2-hydroxyethyl methacrylate (HEMA): 1wt%, and a weight average molecular weight Mw: 70 ten thousand) and 5 parts by mass of additives shown in Table 1 were dispersed in 10 parts by mass of solder particles (trade name: M707 (Sn-3.0Ag-0.5Cu), mp: 217 ℃ C., Kitakutakuai Co., Ltd.) having AN average particle diameter (D50) of 1.1 μ M and conductive particles (resin core, Au plating) having AN average particle diameter (D50) of 5 μ M to prepare AN anisotropic conductive adhesive.
The latent aluminum chelate curing agent was produced as follows. First, 800 parts by mass of distilled water, 0.05 parts by mass of a surfactant (NEWREX (ニューレックス) R-T, Japan fat and oil (Co., Ltd.)), and 4 parts by mass of polyvinyl alcohol (PVA-205, (Co., Ltd.)) as a dispersant were charged into a 3-liter interfacial polymerization vessel equipped with a thermometer, and mixed uniformly. To this mixed solution, 11 parts by mass of a 24% isopropyl alcohol solution of aluminum monoacetylacetonide bis (ethyl acetoacetate) (Alumichelate D, Kawaken Fine Chemicals co., Ltd.) and 11 parts by mass of a trimethylolpropane (1 mol) adduct of methylene diphenyl-4, 4 ́ -diisocyanate (3 mol) (D-109, mitsui chemical corporation) dissolved in 30 parts by mass of ethyl acetate were further charged, emulsified and mixed by a homogenizer (10000rpm/10 minutes), and then interfacial polymerization was performed at 60 ℃ for 6 hours. After the reaction, the polymerization reaction solution was cooled to room temperature, and the interfacial polymer particles were separated by filtration and dried naturally to obtain 20 parts by mass of a spherical latent aluminum chelate curing agent having a particle size of about 10 μm.
[ Table 1]
[ measurement of reaction initiation temperature and reaction Peak temperature of Anisotropic conductive adhesive ]
The reaction initiation temperature (also referred to as heat generation initiation temperature) and the reaction peak temperature (also referred to as heat generation peak temperature) of the anisotropic conductive adhesive were measured at a temperature increase rate of 10 ℃/min using a Differential Scanning Calorimeter (DSC) (DSC6200, Seiko Instruments Inc.). In the curing characteristics, the reaction start temperature refers to the curing start temperature, the reaction peak temperature refers to the temperature at which curing is most active, the reaction end temperature refers to the curing end temperature, and the peak area refers to the amount of heat generation.
[ evaluation of Life time ]
The initial heat generation amount of the anisotropic conductive adhesive and the heat generation amount when the anisotropic conductive adhesive was left at room temperature for 96 hours were measured using a Differential Scanning Calorimeter (DSC) (DSC6200, Seiko Instruments Inc.). When the amount of heat generation was reduced by 20% or more when the sheet was left at room temperature for 96 hours, the life defect was evaluated as "x", and when the amount of heat generation was reduced by less than 20%, the life good was evaluated as "o".
[ production of LED mounting sample ]
As shown in fig. 5, an LED mounting sample was produced. A plurality of 50 μm pitch wiring substrates (50 μm Al wiring-25 μm PI (polyimide) layer-50 μm Al foundation) 51 were arranged on a stage, and about 10 μ g of the anisotropic conductive adhesive 50 was coated on each wiring substrate 51. An LED chip (trade name: DA3547, Cree corporation (maximum rating: 150mA, size: 0.35 mm. times.0.46 mm))52 was mounted on the anisotropic conductive adhesive 50, and flip chip mounting was performed using a hot press 53 under the conditions of the apparatus A for 180 ℃ to 2N to 10 seconds or the apparatus B for 180 ℃ to 2N to 30 seconds, to obtain an LED mounting sample.
Fig. 6 is a graph showing temperature profiles of 180 c-10 seconds and 180 c-30 seconds. As shown in fig. 6, since the temperature rise curve of device a is steeper than that of device B, it is difficult for device a to obtain a larger wafer shear strength or peel strength than that of device B.
[ measurement of shear Strength of wafer ]
As shown in FIG. 7, the bonding strength of each LED mounting sample was measured using a wafer shear tester under the conditions of a shear speed of the tool 54 of 20 μm/sec at 25 ℃. The bonding strength of 4 LED mounting samples was measured, and the average value thereof was calculated.
[ measurement of peeling Strength ]
An anisotropic conductive adhesive 60 was applied to a white ceramic plate 61 with a thickness of 100 μm, and a 1.5mm × 10mm aluminum sheet 62 was thermocompression bonded to the ceramic plate 61 under the conditions of the apparatus A for 180 ℃ -1.5N-10 seconds or the apparatus B for 180 ℃ -1.5N-30 seconds, thereby producing a bonded body.
As shown in fig. 8, the aluminum sheet 62 of the joined body was peeled in the 90 ° Y-axis direction at a drawing speed of 50 mm/sec using Tensilon, and the maximum value of the peel strength required for the peeling was measured. The maximum value of the peel strength of the 4 samples was measured, and the average value thereof was calculated.
< example 1 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive A (3-mercaptopropyltrimethoxysilane). The reaction start temperature of the anisotropic conductive adhesive was 78 deg.c and the reaction peak temperature was 135 deg.c. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 2 >
0.5 part by mass of additive B (3-mercaptopropylmethyldimethoxysilane) was added to prepare an anisotropic conductive adhesive. The reaction start temperature of the anisotropic conductive adhesive was 70 ℃ and the reaction peak temperature was 132 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 3 >
1 part by mass of additive B (3-mercaptopropylmethyldimethoxysilane) was added to prepare an anisotropic conductive adhesive. The reaction start temperature of the anisotropic conductive adhesive was 78 deg.c and the reaction peak temperature was 137 deg.c. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 4 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive C (hydrogenated episulfide). The reaction start temperature of the anisotropic conductive adhesive was 75 ℃ and the reaction peak temperature was 131 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 5 >
An anisotropic conductive adhesive was prepared by blending 2 parts by mass of additive C (hydrogenated episulfide). The reaction start temperature of the anisotropic conductive adhesive was 75 ℃ and the reaction peak temperature was 138 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 6 >
An anisotropic conductive adhesive was prepared by blending 5 parts by mass of additive C (hydrogenated episulfide). The reaction start temperature of the anisotropic conductive adhesive was 76 ℃ and the reaction peak temperature was 157 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 7 >
An anisotropic conductive adhesive was prepared by blending 10 parts by mass of additive C (hydrogenated episulfide). The reaction start temperature of the anisotropic conductive adhesive was 76 ℃ and the reaction peak temperature was 170 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 8 >
An anisotropic conductive adhesive was prepared by blending 40 parts by mass of additive C (hydrogenated episulfide). The reaction start temperature of the anisotropic conductive adhesive was 76 ℃ and the reaction peak temperature was 176 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 9 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive D (1, 4-bis (3-mercaptobutyryloxy) butane). The reaction start temperature of the anisotropic conductive adhesive was 73 ℃ and the reaction peak temperature was 153 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 10 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive E (pentaerythritol tetrakis (3-mercaptobutyrate)). The reaction start temperature of the anisotropic conductive adhesive was 68 ℃ and the reaction peak temperature was 158 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< example 11 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive F (pentaerythritol tetrakis (3-mercaptopropionate)). The reaction start temperature of the anisotropic conductive adhesive was 75 ℃ and the reaction peak temperature was 155 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< comparative example 1 >
An anisotropic conductive adhesive was prepared without adding additives. The reaction start temperature of the anisotropic conductive adhesive was 60 ℃ and the reaction peak temperature was 102 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< comparative example 2 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive G (3-glycidoxypropyltrimethoxysilane). The reaction start temperature of the anisotropic conductive adhesive was 60 ℃ and the reaction peak temperature was 102 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< comparative example 3 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive H (3-glycidoxypropyltriethoxysilane). The reaction start temperature of the anisotropic conductive adhesive was 60 ℃ and the reaction peak temperature was 102 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< comparative example 4 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive I (3-methacryloxypropylmethyldimethoxysilane). The reaction start temperature of the anisotropic conductive adhesive was 60 ℃ and the reaction peak temperature was 102 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
< comparative example 5 >
An anisotropic conductive adhesive was prepared by blending 1 part by mass of additive J (3-methacryloxypropyltrimethoxysilane). The reaction start temperature of the anisotropic conductive adhesive was 60 ℃ and the reaction peak temperature was 102 ℃. Table 2 shows the evaluation results of lifetime, the measurement results of wafer shear strength, and the measurement results of peel strength.
[ Table 2]
As in comparative examples 1 to 5, when no nucleophilic compound containing a sulfur atom having an unshared electron pair was blended, the evaluation result of the lifetime was poor, and the shear strength and peel strength of the wafer when pressure bonding was performed using the apparatus A having a steep temperature rise curve were lower than those when pressure bonding was performed using the apparatus B.
On the other hand, as in examples 1 to 11, when a nucleophilic compound containing a sulfur atom having an unshared electron pair was blended, the evaluation result of the lifetime became good, and the shear strength and peel strength of the wafer when pressure bonding was performed using the apparatus a having a steep temperature rise curve were not changed from those when pressure bonding was performed using the apparatus B. That is, it is understood from examples 1 to 11 that excellent life performance and a wide mounting range can be obtained by increasing the stability of the aluminum chelate compound-silanol-based curing catalyst and delaying the curing reaction.
< embodiment 2 >
In example 2, the LED mounting samples mounted on the apparatus B for 180 ℃ to 2N to 30 seconds in examples 1 and 4 and comparative examples 1 and 2 were evaluated for conductivity and heat release property.
[ evaluation of conductivity ]
The on-resistance of each LED mounting sample was measured at the initial stage and after a Thermal Cycle Test (TCT). In the cooling-heating cycle test, the LED mounting sample was exposed to an environment of-40 ℃ and 100 ℃ for 30 minutes each, and this cooling-heating cycle was performed for 1000 cycles, taking this as 1 cycle. For the evaluation of the conductivity, Vf values were measured when If =50mA, and a case where the increase in Vf value was less than 0.1V compared to Vf values in the test result table was indicated as "o", and a case where Vf value was 0.1V or more was indicated as "x".
[ evaluation of exothermic Properties ]
The thermal resistance of each LED mounting sample was measured at the initial stage and after a Thermal Cycle Test (TCT). In the cooling-heating cycle test, the LED-mounted sample was exposed to an environment of-40 ℃ and 100 ℃ for 30 minutes each, and this was set as 1 cycle, and the cooling-heating cycle was performed for 1000 cycles, as in the evaluation of conductivity. The thermal resistance was measured using a transient thermal resistance measuring device (coat Electronics co., Ltd) in a dynamic manner. The measurement conditions were carried out under If =50mA and Im =1mA, and the thermal resistance value (K/W) of the LED package at 0.1 second of lighting was read. The evaluation of the heat release property was that the case where the change in the thermal resistance value was less than 2 ℃ was described as "O", and the case where the change in the thermal resistance value was 2 ℃ or more was described as "X".
< examples 1 and 4, comparative examples 1 and 2 >
Table 3 shows the results of the evaluation of the conductivity and heat release of examples 1 and 4 and comparative examples 1 and 2.
[ Table 3]
| Example 1 | Example 4 | Comparative example 1 | Comparative example 2 | |
| Additive agent | A | C | Is free of | G |
| Addition amount [ parts by mass] | 1 | 1 | Is free of | 1 |
| Curing condition at 180 |
30 |
30 |
30 |
30 seconds |
| Evaluation of conductivity | ○ | ○ | ○ | ○ |
| Evaluation of exothermic Properties | ○ | ○ | × | × |
As in comparative examples 1 and 2, when the nucleophilic compound containing a sulfur atom having an unshared electron pair was not blended, the evaluation of the conductivity was good, but the evaluation of the heat release property was poor. On the other hand, as in examples 1 and 4, when a nucleophilic compound containing a sulfur atom having an unshared electron pair is blended, the evaluation of conductivity and the evaluation of heat release were good. By measuring the exothermic property, it is possible to detect a minute change in the mounting state which cannot be known in the shear strength, peel strength, and on-resistance of the wafer.
Description of the symbols
11 wiring
11a oxide film
12 epoxy compound sea
Islands of 13 acrylic resin
21 substrate
22 wiring pattern
23 light emitting element
24 n electrode
25 p electrode
26 bump
30 Anisotropic conductive film
50 anisotropic conductive adhesive
51 wiring substrate
52 LED wafer
53 heat pressing tool
54 tool
60 Anisotropic conductive adhesive
61 ceramic plate
62 aluminium sheet
Claims (7)
1. An adhesive composition comprising:
a cationically polymerizable compound,
An aluminum chelate compound-silanol-based curing catalyst, and
a nucleophilic compound containing a sulfur atom having an unshared electron pair,
wherein the nucleophilic compound is an episulfide compound,
the content of the nucleophilic compound is 0.5 to 50 parts by mass per 100 parts by mass of the cationically polymerizable compound.
2. The adhesive composition of claim 1, wherein the aluminum chelate-silanol-based curing catalyst comprises an aluminum chelate curing agent and a silane coupling agent,
the aluminum chelate curing agent is a latent aluminum chelate curing agent which is held in a porous resin obtained by interfacial polymerization of a polyfunctional isocyanate compound.
3. The adhesive composition according to claim 1, wherein the cationically polymerizable compound comprises an alicyclic epoxy compound or a hydrogenated epoxy compound,
the adhesive composition further contains an acrylic resin which is obtained by polymerizing 0.5-10 wt% of acrylic acid and 0.5-10 wt% of acrylate with hydroxyl and has the weight-average molecular weight of 50000-900000.
4. The adhesive composition according to claim 1, wherein the reaction peak temperature at a temperature rise rate of 10 ℃/min of the differential scanning calorimeter is 50 ℃ or higher than the reaction initiation temperature.
5. The adhesive composition as set forth in any one of claims 1 to 4, further comprising: conductive particles having a metal layer formed on the surface of the resin particles, and solder particles having an average particle diameter smaller than that of the conductive particles.
6. A light-emitting device is provided with:
a substrate having a wiring pattern,
An anisotropic conductive film formed on the electrodes of the wiring pattern, and
a light emitting element mounted on the anisotropic conductive film,
the anisotropic conductive film is a film-shaped cured product of an anisotropic conductive adhesive obtained by blending conductive particles into the adhesive composition according to claim 1.
7. The light-emitting device as set forth in claim 6, wherein the wiring pattern of the substrate is made of aluminum.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015-112187 | 2015-06-02 | ||
| JP2015112187 | 2015-06-02 | ||
| PCT/JP2016/066195 WO2016194952A1 (en) | 2015-06-02 | 2016-06-01 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107614650A CN107614650A (en) | 2018-01-19 |
| CN107614650B true CN107614650B (en) | 2021-03-12 |
Family
ID=57440680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680028674.XA Active CN107614650B (en) | 2015-06-02 | 2016-06-01 | Adhesive composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10174225B2 (en) |
| JP (2) | JP6763199B2 (en) |
| KR (1) | KR102055114B1 (en) |
| CN (1) | CN107614650B (en) |
| TW (1) | TWI714592B (en) |
| WO (1) | WO2016194952A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102019468B1 (en) * | 2016-11-29 | 2019-09-06 | 주식회사 엘지화학 | Adhesive film for semiconductor device and semiconductor device |
| CN110662813B (en) * | 2017-07-25 | 2021-09-07 | 大塚化学株式会社 | Adhesive composition and adhesive film |
| KR102444486B1 (en) * | 2018-01-30 | 2022-09-19 | 쇼와덴코머티리얼즈가부시끼가이샤 | Adhesive composition, film adhesive, adhesive sheet, and manufacturing method of a semiconductor device |
| CN111048499B (en) * | 2019-12-16 | 2022-05-13 | 业成科技（成都）有限公司 | Micro light-emitting diode display panel and preparation method thereof |
| KR102291784B1 (en) * | 2019-12-16 | 2021-08-24 | 주식회사 노피온 | Cluster type anisotropic conductive adhesive film containing thermoplastic resin, a method of forming solder bumps and a method of manufacturing a bonded structure using the same |
| JP7319499B2 (en) | 2021-01-14 | 2023-08-02 | 三菱重工業株式会社 | Ammonia decomposition equipment |
| JP2023010105A (en) * | 2021-07-09 | 2023-01-20 | デクセリアルズ株式会社 | Curable composition, and cured product |
| JP2023034355A (en) * | 2021-08-30 | 2023-03-13 | デクセリアルズ株式会社 | Method for manufacturing lens module and thermosetting adhesive |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006316259A (en) * | 2005-04-12 | 2006-11-24 | Sony Chemical & Information Device Corp | Method for producing adhesive |
| JP2015054942A (en) * | 2013-09-13 | 2015-03-23 | デクセリアルズ株式会社 | Adhesive and light-emitting device |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07316440A (en) * | 1994-03-30 | 1995-12-05 | Kansai Paint Co Ltd | Water-base curable resin composition |
| JP2002212537A (en) * | 2001-01-24 | 2002-07-31 | Sony Chem Corp | Adhesive and electric device |
| JP3875859B2 (en) * | 2001-06-27 | 2007-01-31 | ソニーケミカル＆インフォメーションデバイス株式会社 | Curing agent particles, method for producing curing agent particles, and adhesive |
| US6891017B2 (en) * | 2001-06-29 | 2005-05-10 | Essilor International Compagnie General D'optique | Fast polymerizable/curable episulfide based composition, polymerization/curing process and optical articles resulting therefrom |
| JP4381255B2 (en) * | 2003-09-08 | 2009-12-09 | ソニーケミカル＆インフォメーションデバイス株式会社 | Latent curing agent |
| US20070096396A1 (en) * | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
| JP5707662B2 (en) | 2008-01-25 | 2015-04-30 | デクセリアルズ株式会社 | Thermosetting epoxy resin composition |
| JP2014065766A (en) | 2012-09-24 | 2014-04-17 | Dexerials Corp | Anisotropic conductive adhesive |
| US9062162B2 (en) * | 2013-03-15 | 2015-06-23 | Prc-Desoto International, Inc. | Metal ligand-containing prepolymers, methods of synthesis, and compositions thereof |
-
2016
- 2016-06-01 JP JP2016110103A patent/JP6763199B2/en active Active
- 2016-06-01 WO PCT/JP2016/066195 patent/WO2016194952A1/en active Application Filing
- 2016-06-01 CN CN201680028674.XA patent/CN107614650B/en active Active
- 2016-06-01 KR KR1020177029182A patent/KR102055114B1/en active IP Right Grant
- 2016-06-01 US US15/579,050 patent/US10174225B2/en active Active
- 2016-06-02 TW TW105117312A patent/TWI714592B/en active
-
2020
- 2020-09-08 JP JP2020150556A patent/JP6977839B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006316259A (en) * | 2005-04-12 | 2006-11-24 | Sony Chemical & Information Device Corp | Method for producing adhesive |
| JP2015054942A (en) * | 2013-09-13 | 2015-03-23 | デクセリアルズ株式会社 | Adhesive and light-emitting device |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016194952A1 (en) | 2016-12-08 |
| JP2016222917A (en) | 2016-12-28 |
| TWI714592B (en) | 2021-01-01 |
| KR102055114B1 (en) | 2019-12-12 |
| US10174225B2 (en) | 2019-01-08 |
| US20180171184A1 (en) | 2018-06-21 |
| KR20170127017A (en) | 2017-11-20 |
| CN107614650A (en) | 2018-01-19 |
| JP2021004363A (en) | 2021-01-14 |
| JP6977839B2 (en) | 2021-12-08 |
| JP6763199B2 (en) | 2020-09-30 |
| TW201714909A (en) | 2017-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107614650B (en) | Adhesive composition | |
| KR102513546B1 (en) | Anisotropic conductive film | |
| CN100489048C (en) | Binder composition for semiconductor device and binder sheet for semiconductor device | |
| EP2500932B1 (en) | Adhesive composition | |
| US20030111519A1 (en) | Fluxing compositions | |
| WO2011129372A1 (en) | Curable resin composition, adhesive epoxy resin paste, die-bonding agent, non-conductive paste, adhesive epoxy resin film, non-conductive epoxy resin film, anisotropic conductive paste, and anisotropic conductive film | |
| JP5153597B2 (en) | Protective film forming sheet for chip and semiconductor chip with protective film | |
| US9390831B2 (en) | Electronic device using anisotropic conductive composition and film | |
| KR102363322B1 (en) | anisotropic conductive film | |
| WO2017119274A1 (en) | Adhesive composition | |
| KR102036570B1 (en) | Circuit connection material, and manufacturing method for assembly using same | |
| JP2021185579A (en) | Conductive material and connection structure | |
| KR20020091216A (en) | Stabilized Cationically Polymerizable Composition, and Adhesive Film and Conductor Circuit Comprising the Same | |
| KR101035873B1 (en) | Fast curable adhesive film composition at high temperature and adhesive film using it | |
| CN108456501B (en) | Conductive adhesive composition | |
| JP7172990B2 (en) | Adhesive composition and structure | |
| KR100727550B1 (en) | Adhesive composition and adhesive sheet for semiconductor device | |
| JP6181825B2 (en) | Anisotropic conductive film and method of manufacturing mounting body using the same | |
| TWI704581B (en) | Conductive material and connection structure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |